2,7-bis(methyldiethoxyphosphonate)-9,9-diethylfluorene | 859437-49-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,7-bis(methyldiethoxyphosphonate)-9,9-diethylfluorene
• 英文别名: 2,7-Bis(diethoxyphosphorylmethyl)-9,9-diethylfluorene
• CAS: 859437-49-3
• 化学式: C₂₇H₄₀O₆P₂
• 分子量: 522.559
• InChiKey: BLXPIQQJKRHHCS-UHFFFAOYSA-N

物化性质

• 沸点：
  617.3±55.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,7-bis(methyldiethoxyphosphonate)-9,9-diethylfluorene 、 对硝基苯甲醛 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 30.0h， 以0.73 g的产率得到9,9-diethyl-2,7-bis[2-(4-nitrophenyl)vinyl]-9H-fluorene
  参考文献：
  名称：

  Synthesis of Two-Photon Absorbing Unsymmetrical Branched Chromophores through Direct Tris(bromomethylation) of Fluorene

  摘要：

  Branched fluorene-based chromophores bearing electron-donating diphenylamino or electron-withdrawing nitro groups were synthesized as well as their linear analogues. An efficient synthetic method was developed via a novel 2,4,7-tris(bromomethyl)-9,9-diethylfluorene intermediate. The bromomethyl groups in this key intermediate were converted to either phosphonate or carboxaldehyde moieties, facilitating preparation of a high functionality branched structure. It was found that the reactivity at position 4 is attenuated in the bromomethyl and phosphorylated derivates, facilitating the selective and systematic functionalization of the fluorenyl system. All compounds were stable up to ca. 350 degrees C, except for a sterically crowded branched derivative. The linear optical properties of the compounds were investigated by UV-visible, steady-state fluorescence, and excitation anisotropy spectroscopic measurements. Fluorescence quantum yields were greater than or equal to 0.84 for symmetric linear and unsymmetric branched derivatives. Very high two-photon absorption (2PA) cross-sections were achieved (5765 GM at 520 nm and 4194 GM at 570 nm), as determined with use of picosecond and femtosecond laser excitation sources, respectively.

  DOI：

  10.1021/jo0503512
• 作为产物：
  描述：

  2,7-二溴-9,9-二乙基芴 在 正丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2,7-bis(methyldiethoxyphosphonate)-9,9-diethylfluorene
  参考文献：
  名称：

  Electroluminescent Properties of Novel Fluorene Derivatives with Aromatic Amine Moieties

  摘要：

  2,7-Bis[(4-diphenylamino)phenylvinylene]-9,9-diethylfluorene(BDPDF, 1) and 2,7-bis[(9-ethyl-3-carbazolylvinylene)-9,9-diethylfluorene(BECDF, 2) have been synthesized and characterized. To evaluate electroluminescent performance, compound 1 and 2 were used as emitting materials and dopant materials, respectively and the basic device structure was ITO/m-MTDATA/a-NPD/1 or 2 or doped DPVBi with 1 or 2/Alq 3 /LiF/Al.The devices using BDPDF(1) and BECDF(2) show EL peak at 470 nm and 486 nm. The device showed a blue light-emission with the CIE chromaticity coordinates of (0.177, 0.268).

  DOI：

  10.1080/15421400500365292

文献信息

• Highly Efficient Blue-Light-Emitting Diodes Based on Styrylamine Derivatives End-capped with a Diphenylvinyl Group
  作者：Seul-Ong Kim、Kum-Hee Lee、Sun-Woo Kang、Jin-Yong Lee、Ji-Hoon Seo、Young-Kwan Kim、Seung-Soo Yoon

  DOI：10.5012/bkcs.2010.31.02.389

  日期：2010.2.20

  In this paper, we reported the synthesis and electroluminescent properties of blue fluorescent styrylamine derivatives end-capped with a diphenylvinyl group. A new series of styrylamine derivatives have been synthesized via the HornerWadsworth-Emmons reaction. To explore electroluminescent properties of these molecules, multilayer organic lightemitting devices with the configuration of ITO/NPB/1-5

  在本文中，我们报道了用二苯基乙烯基封端的蓝色荧光苯乙烯胺衍生物的合成和电致发光性质。通过 HornerWadsworth-Emmons 反应合成了一系列新的苯乙烯胺衍生物。为了探索这些分子的电致发光特性，制造了具有ITO / NPB / 1-5掺杂在MADN / Bphen / Liq / Al中的多层有机发光器件。所有器件都表现出具有良好 EL 性能的蓝色发射。在本文报道的那些中，使用掺杂剂 5 的器件在 11.0 V 时表现出 24,000 cd/m 2 的最大亮度，在 20 mA/cm 2 时的发光效率为 12.5 cd/A，在 20 mA 时的功率效率为 6.50 lm/W /cm 2 和CIEx,y坐标（x = 0.173, y = 0.306）在8.0 V时，所有这些都证明了这些材料在蓝色OLED中的优越性。
• <i>N</i>-Arylpyrrole-Based Chromophores of Donor-π-Donor Type Displaying High Two-Photon Absorption
  作者：Qianqian Li、Jing Huang、Aoshu Zhong、Cheng Zhong、Ming Peng、Jun Liu、Zhiguo Pei、Zhenli Huang、Jingui Qin、Zhen Li

  DOI：10.1021/jp111919z

  日期：2011.4.21

  A series of new N-arylpyrrole-based chromophores with the donor-pi-donor structure have been designed and synthesized via Wittig-Homer-Emmons olefination and Suzuki coupling reactions. The electronic and optical properties of the designed chromophores could be well tuned by modifying the conjugation bridges and changing the groups linked to the pyrrole moieties through the C-N single bond. All the chromophores exhibited two-photon absorption activity in the range of 730-900 nm with a large two-photon absorption cross section (similar to 1000-1700 GM).
• Electroluminescent Properties of Novel Fluorene Derivatives with Aromatic Amine Moieties
  作者：Kwang-Yol Kay、Jung-Hoon Kim、Sun-Ho Kim、Ho-Cheol Park、Jong-Wook Park

  DOI：10.1080/15421400500365292

  日期：2006.2.1

  2,7-Bis[(4-diphenylamino)phenylvinylene]-9,9-diethylfluorene(BDPDF, 1) and 2,7-bis[(9-ethyl-3-carbazolylvinylene)-9,9-diethylfluorene(BECDF, 2) have been synthesized and characterized. To evaluate electroluminescent performance, compound 1 and 2 were used as emitting materials and dopant materials, respectively and the basic device structure was ITO/m-MTDATA/a-NPD/1 or 2 or doped DPVBi with 1 or 2/Alq 3 /LiF/Al.The devices using BDPDF(1) and BECDF(2) show EL peak at 470 nm and 486 nm. The device showed a blue light-emission with the CIE chromaticity coordinates of (0.177, 0.268).
• Synthesis of Two-Photon Absorbing Unsymmetrical Branched Chromophores through Direct Tris(bromomethylation) of Fluorene
  作者：Sheng Yao、Kevin D. Belfield

  DOI：10.1021/jo0503512

  日期：2005.6.1

  Branched fluorene-based chromophores bearing electron-donating diphenylamino or electron-withdrawing nitro groups were synthesized as well as their linear analogues. An efficient synthetic method was developed via a novel 2,4,7-tris(bromomethyl)-9,9-diethylfluorene intermediate. The bromomethyl groups in this key intermediate were converted to either phosphonate or carboxaldehyde moieties, facilitating preparation of a high functionality branched structure. It was found that the reactivity at position 4 is attenuated in the bromomethyl and phosphorylated derivates, facilitating the selective and systematic functionalization of the fluorenyl system. All compounds were stable up to ca. 350 degrees C, except for a sterically crowded branched derivative. The linear optical properties of the compounds were investigated by UV-visible, steady-state fluorescence, and excitation anisotropy spectroscopic measurements. Fluorescence quantum yields were greater than or equal to 0.84 for symmetric linear and unsymmetric branched derivatives. Very high two-photon absorption (2PA) cross-sections were achieved (5765 GM at 520 nm and 4194 GM at 570 nm), as determined with use of picosecond and femtosecond laser excitation sources, respectively.